N-Acetylmuramic acid

N-Acetylmuramic acid, "NAM" or MurNAc, is the addition of phosphoenolpyruvate and N-acetylglucosamine with the chemical formula C
11
H
19
NO
8
. It is a key builder of peptidoglycan in the bacterial cell wall, which is built from alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc), cross-linked by oligopeptides at the lactic acid residue of MurNAc.

N-Acetylmuramic acid
N-Acetylmuramic acid.svg
Names
Preferred IUPAC name
(2R)-2-{[(2R,3R,4R,5S,6R)-3-Acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.031.092 Edit this at Wikidata
UNII
  • InChI=1S/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1 ☒N
    Key: MNLRQHMNZILYPY-MKFCKLDKSA-N ☒N
  • InChI=1/C11H19NO8/c1-4(10(16)17)19-9-7(12-5(2)14)11(18)20-6(3-13)8(9)15/h4,6-9,11,13,15,18H,3H2,1-2H3,(H,12,14)(H,16,17)/t4-,6-,7-,8-,9-,11?/m1/s1
    Key: MNLRQHMNZILYPY-MKFCKLDKBR
  • O=C(O)[C@H](O[C@H]1[C@H](O)[C@H](OC(O)[C@@H]1NC(=O)C)CO)C
Properties
C11H19NO8
Molar mass 293.272 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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MurNAc is a monosaccharide derivative of N-acetylglucosamine.

Formation of NAMEdit

NAM is a combination of N-acetylglucosamine and phosphoenolpyruvate (PEP). This addition happens exclusively in the cell cytoplasm.

Clinical significanceEdit

N-Acetylmuramic acid (MurNAc) is part of the peptidoglycan polymer of bacterial cell walls. MurNAc is covalently linked to N-acetylglucosamine and may also be linked through the hydroxyl on carbon number 4 to the carbon of L-alanine. A pentapeptide composed of L-alanyl-D-isoglutaminyl-L-lysyl-D-alanyl-D-alanine is added to the MurNAc in the process of making the peptidoglycan strands of the cell wall.

Synthesis is inhibited by fosfomycin.[1]

NAG and NAM cross-linking can be inhibited by antibiotics to inhibit pathogens from growing within the body. Therefore, both NAG and NAM are valuable polymers in medicinal research.

ReferencesEdit

  1. ^ Grif K, Dierich MP, Pfaller K, Miglioli PA, Allerberger F (2001). "In vitro activity of fosfomycin in combination with various antistaphylococcal substances". Journal of Antimicrobial Chemotherapy. 48 (2): 209–217. doi:10.1093/jac/48.2.209. PMID 11481290.

See alsoEdit